For research use only. Not for therapeutic Use.
Tebuquine (Cat.No:I009734), also known CI-897 and WR-228258, is an antimalarial agent. WR-225,448 is active against P. falciparum in vitro. WR 228,258 in vitro shows a chloroquine-like effect, but not in vivo, suggesting that its mode of action in vivo is different from that of chloroquine. WR 225,448 has no action in the CIPC in vitro and affects primarily mitochondria of the parasites in vivo. It probably acts through a metabolite. Both pre-erythrocytic and erythrocytic stages of rodent malaria parasites are affected by WR 225,448.
| Catalog Number | I009734 |
| CAS Number | 74129-03-6 |
| Synonyms | Tebuquine; CI-897; CI897; CI 897; WR-228,258; WR 228,258; WR228,258; WR-228258; WR 228258; WR228258.;(1,1/’-Biphenyl)-2-ol, 4/’-chloro-5-((7-chloro-4-quinolinyl)amino)-3-(((1,1-dimethylethyl)amino)methyl)- |
| Molecular Formula | C26H25Cl2N3O |
| Purity | ≥95% |
| Solubility | Soluble in DMSO |
| Storage | 0 - 4 °C for short term, or -20 °C for long term |
| IUPAC Name | 2-[(tert-butylamino)methyl]-6-(4-chlorophenyl)-4-[(7-chloroquinolin-4-yl)amino]phenol |
| InChI | InChI=1S/C26H25Cl2N3O/c1-26(2,3)30-15-17-12-20(14-22(25(17)32)16-4-6-18(27)7-5-16)31-23-10-11-29-24-13-19(28)8-9-21(23)24/h4-14,30,32H,15H2,1-3H3,(H,29,31) |
| InChIKey | BCHMRNALCJISMZ-UHFFFAOYSA-N |
| SMILES | CC(C)(C)NCC1=C(C(=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)C4=CC=C(C=C4)Cl)O |
| Reference | </br>1:Exploration of rate-limiting conformational state for 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1/’-biphenyl]-2-ols and N(omega)-oxides (tebuquine analogues) for antimalarial activity using molecular shape analysis and molecular field analysis studies. Sharma P, Chhabra S, Rai N, Ghoshal N.J Chem Inf Model. 2007 May-Jun;47(3):1087-96. Epub 2007 Apr 11. PMID: 17425301 </br>2:Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues. O/’Neill PM, Willock DJ, Hawley SR, Bray PG, Storr RC, Ward SA, Park BK.J Med Chem. 1997 Feb 14;40(4):437-48. PMID: 9046333 </br>3:Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1/’-biphenyl]-2-ols and N omega-oxides. Werbel LM, Cook PD, Elslager EF, Hung JH, Johnson JL, Kesten SJ, McNamara DJ, Ortwine DF, Worth DF.J Med Chem. 1986 Jun;29(6):924-39. PMID: 3712383 |
